methyl 4-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7-dihydro-5H-benzocycloheptene-8-carboxylate → 4-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid

HRID 1277262노트

반응식

HRID 1277262 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:16][CH2:15][CH:14]([C:17]3[C:27]4[CH2:26][CH2:25][CH2:24][C:23]([C:28]([O:30]C)=[O:29])=[CH:22][C:21]=4[CH:20]=[CH:19][CH:18]=3)[CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1>C(O)C.C1COCC1.[OH-].[Na+]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH2:12][CH2:13][CH:14]([C:17]3[C:27]4[CH2:26][CH2:25][CH2:24][C:23]([C:28]([OH:30])=[O:29])=[CH:22][C:21]=4[CH:20]=[CH:19][CH:18]=3)[CH2:15][CH2:16]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

참가 물질

4

반응물 1

HCID 18472663methyl 4-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7-dihydro-5H-benzocycloheptene-8-carboxylate

생성물 1

HCID 184723754-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid수율 58.4%

시약·촉매·용매 2

HCID 14798Sodium Hydroxide용매HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

To a solution of methyl 4-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7-dihydro-5H-benzocyclo-heptene-8-carboxylate (1.0 g) in ethanol/THF (20/40 ml) was added at room temperature IN sodium hydroxide solution (2.7 ml), and the mixture was stirred for 13 hours. Under reduced pressure, the mixture was concentrated. To the mixture was added water, and the mixture was washed with ethyl acetate. To the aqueous layer was added 1N hydrochloric acid (5 ml), and the mixture was extracted with ethyl acetate/THF. The organic layer was washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the resulting colorless crystals were collected by filtration, which were washed with hexane to give colorless crystals of 4-[1-(4-methylphenylsulfonyl)piperidin-4-yl]-6,7-dihydro-5H-benzocycloheptene-8-carboxylic acid (565.4 mg).

후처리

  1. concentrationUnder reduced pressure, the mixture was concentrated
  2. additionTo the mixture was added water
  3. washthe mixture was washed with ethyl acetate
  4. additionTo the aqueous layer was added 1N hydrochloric acid (5 ml)
  5. extractionthe mixture was extracted with ethyl acetate/THF
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried with magnesium sulfate
  8. concentrationUnder reduced pressure, the mixture was concentrated
  9. filtrationthe resulting colorless crystals were collected by filtration, which
  10. washwere washed with hexane

출처 및 근거

ORD 기록
ord-4327a161f4ce47d0909747a0440cfcbe
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06166006

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